BIP! Finder - 1H NMR Dynamic study of thermal Z/E isomerization of 5-substituted 2-alkylidene-4-oxothiazolidine derivatives: Barriers to rotation about CC bond

2006 • 1H NMR Dynamic study of thermal Z/E isomerization of 5-substituted 2-alkylidene-4-oxothiazolidine derivatives: Barriers to rotation about CC bond

Authors: Marković, R., Baranac-Stojanović, Marija, Juranić, N., Macura, S., Cekic, I., Minić, Dragica M.

Venue: Journal of Molecular Structure

Type: Publication

Abstract: The rotational barriers between the configurational isomers of two structurally related push-pull 4-oxothiazolidines, differing in the number of exocyclic C=C bonds, have been determined by dynamic H-1 NMR spectroscopy. The equilibrium mixture of (5-ethoxy-carbonylmethyl-4-oxothiazolidin-2-ylidene)-1-phenylethanone (1a) in CDCl3 at room temperature to 333 K consists of the E- and Z-isomers which are separated by an energy barrier Delta G(#) 98.5 kJ/mol (at 298 K). The variable-temperature H-1 NMR data for the isomerization of ethyl (5-ethoxycar... (read more)

Topics: Stereochemistry Crystallography Computational chemistry

DOI: 10.1016/j.molstruc.2006.03.075

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